When I pass, I'd like my ashes turned into precious stones for my kids. Yes, that’s a thing. About a ½ cup of cremated remains can create 4-5 gemstones. Just enough to piss someone off. Hoping that they’re all close to the same color for everyone’s sake.

Not the point. I'm not quite certain anyone knows this. If I were to pass suddenly, my wife will try to bury me, my son knows that I'd like to be cremated after any usable organs are donated, and I'm not quite sure how my daughters will react. If this were to happen, you can see the possible points of contention and conflict brewing in my own family.

This scenario isn't unique. According to the American Bar Association, 70% of family disputes during estate settlement stem from undocumented wishes and assumptions about what the deceased "would have wanted."

A 2023 study by Wealth Counsel found that families who had documented conversations about non-financial wishes were 60% less likely to experience lasting relationship damage during the probate process.

Yet another study revealed that the average family makes over 40 assumptions about their loved one's end-of-life preferences—and gets more than half of them wrong.

The solution isn't more legal documents—it's more questions.

Most families operate on a foundation of loving assumptions. We think we know what matters to our parents, spouses, and siblings because we've lived alongside them for years or decades. However, what's fascinating is that the deeper our relationships, the more likely we are to fill in gaps with our own projections rather than asking direct questions.

That "weird" conversation you've been avoiding—about the cats, the garden, the family photos, or yes, even turning ashes into gemstones—isn't awkward. It's enlightening. What seems perfectly obvious to you might be a complete surprise to your family members, and vice versa.

These conversations are gifts. They're opportunities to truly know your loved ones, rather than just thinking you know them. When you ask the questions nobody else is asking, you often discover the most meaningful aspects of what someone values, fears, or dreams about for their legacy.

This is the dangerous space between "I thought you'd want..." and "I never said that." We create assumptions based on casual comments, cultural norms, or what we would want in similar situations. Over time, these assumptions crystallize into "facts" in our minds.

The antidote? Turn every assumption into a question. Instead of thinking "Mom would want a simple funeral," ask "Mom, what does 'simple' mean to you for a funeral?" The specifics matter enormously and are rarely what we expect.

Ironically, the people we're closest to are often the hardest to have these conversations with. We worry about seeming morbid, pushy, or like we're "rushing" someone toward death. We tell ourselves we have plenty of time, or that bringing up these topics will cause unnecessary anxiety.

But intimate relationships require more explicit communication, not less. Your spouse may feel comfortable sharing wishes with you that they'd never tell their children. Your adult kids might assume you've told your spouse things you've never discussed. The solution is creating safe spaces for these revelations within your closest relationships.

There's a world of difference between curious discovery conversations and crisis management. Prevention happens when everyone is healthy and thinking clearly. It's exploratory, even fun. You can laugh about unexpected wishes, ask follow-up questions, and create documentation together.

Reactive conversations happen during medical emergencies, after diagnosis, or worse, after someone has passed. They're fraught with emotion, time pressure, and legal implications. Family members are stressed, grieving, and making assumptions under pressure. This is when conflicts explode.

These seemingly "minor" topics create some of the most explosive family conflicts because nobody thinks to discuss them in advance:

End-of-Life Specifics: Cremation vs. burial preferences, what to do with remains, organ donation timing and limitations, medical intervention boundaries, and funeral service style preferences.

Digital Legacy: Access to photos, social media accounts, email, and online financial accounts. Who has passwords, and what should be preserved vs. deleted?

Pet Care: Arrangements for beloved animals, including special medical needs, behavioral quirks, and end-of-life decisions for elderly pets.

Personal Belongings: Distribution of family heirlooms, handling of personal items like journals or letters, and disposal of potentially embarrassing materials.

Living Arrangements: Preferences for care locations during illness, which family member they'd want to live with, and facility preferences.

Professional Legacy: Business succession, professional reputation management, and ongoing commitments or contracts.

Financial Surprises: Charitable giving priorities, beneficiaries beyond the obvious, and accounts family members don't know about.

Sentimental Wishes: Special items with hidden significance, traditions they want continued, and meaningful ways to be remembered.

Eleanor seemed like a typical cat lover with four pets. After she passed suddenly, her family discovered these weren't just pets—they were elderly cats with complex medical conditions requiring daily medications costing $400 monthly. Her son lived in a no-pets apartment, her daughter was severely allergic, and her sister assumed "someone else" would handle it.

Eleanor had been secretly funding a cat sanctuary in her will, but the family didn't find that document for three weeks. During that chaotic period, one cat had to be euthanized due to untreated diabetes, vet bills mounted to $1,200, and family members stopped speaking over who was "responsible" for the animals their mother "should have known" they couldn't care for. One conversation about her pets could have prevented both animal suffering and family fractures.

When Robert had a stroke, his family focused on selling his house to fund his care. They hired a crew to clear out his "garden hobby," unknowingly destroying $50,000 worth of rare hybrid roses he'd spent decades developing. Only when the American Rose Society called about his scheduled magazine interview did they learn he was internationally recognized, had been featured in Smithsonian Magazine, and was negotiating with a university to establish a research garden bearing his name.

The landscapers had already hauled everything to the dump. Three botanical institutions with purchase agreements for his specimens are now suing the family. Robert's life's work—and his family's financial security—disappeared because no one thought to ask about the significance of his "hobby."

Linda's pearl necklace seemed straightforward—a family heirloom passed down through generations. Both daughters "knew" they would inherit it, each for different reasons. The eldest shared her great-grandmother's name; the younger had always complimented it and remembered her mother saying "someday this will be yours" during wedding planning.

The conflict escalated when Linda's teenage granddaughter posted on social media: "Finally got great-grandma's pearls that were always promised to me!" The younger daughter screenshotted this as "evidence" of family conspiracy. The battle now involves four family members, two lawyers, and a forensic jewelry appraiser who revealed the pearls are worth $15,000, not the assumed $500. Legal fees have exceeded the necklace's value, Christmas gatherings have been canceled for two years, and grandchildren have chosen sides. The necklace sits in a safety deposit box while the family relationship crumbles—all over assumptions about casual comments from a dying woman.

The beautiful truth about these conversations is that they almost always bring families closer together, not further apart. When you learn that your practical father secretly wants a celebration of life with jazz music, or that your minimalist mother has strong feelings about which grandchild should receive her wedding ring, you're not just preventing conflict—you're discovering who your loved ones are.

Don't assume anything until you ask. Those "weird" questions you've been avoiding might be the most enlightening conversations you'll ever have. What seems obvious to you could be completely surprising to them, and their actual wishes might be more interesting, touching, or unexpected than anything you could have imagined.

Start today. Download our Family Conversation Starter Guide below and choose one "assumption" to turn into a question this week. The goal isn't to have every conversation at once—it's to begin the ongoing dialogue that prevents conflicts and deepens relationships.

The most important legacy you can create isn't in your will—it's in the understanding between you and the people you love.

Next Issue: "What family stories do you want preserved, and who's responsible for keeping them alive?"